Our second week in Y Combinator, we almost pivoted away from building a B2B startup. As we walked up a hill on our way to office hours, my co-founder turned to me and said, "What are we doing here? I want to build something my mom can use." So we pivoted to a mobile app for local events.
Our friends, well-intentioned but misguided, feigned enthusiasm and acted supportive of our new direction. The YC partners, who had seen another startup crash and burn in the previous batch with a nearly-identical idea, politely tried to steer us back to our original idea.
Nobody got through to us until Paul Graham found words sharp enough to pierce our mental armor. During office hours with Sam Altman, Sam told us we were about to make a huge mistake, said "Let me get PG," and darted out to the next room. Uh oh. Paul Graham came running into our tiny conference room, obviously irritated, and said:
"Moments like these make me glad we invested in sixty-four startups!" He threw up his hands in exasperation. "If you want to drive off a cliff, go right ahead."
Later, he told us we were "like moths for bad ideas." Oof.
That was enough to pop our bubble. We sucked it up and went back to the hard work of building a B2B company. Paul Graham later said that was the meanest thing he had said to a startup. But in retrospect, it was actually one of the nicest things anybody did for us.
Giving blunt, unfiltered feedback is one of the secrets to Y Combinator's success. And that same brutal honesty is seems to be at the core of many of the greatest technology companies like Apple, Google, and Microsoft. Steve Jobs described his role at Apple as:
I don’t think I run roughshod over people, but if something sucks, I tell people to their face. It’s my job to be honest. I know what I’m talking about, and I usually turn out to be right. That’s the culture I tried to create. We are brutally honest with each other, and anyone can tell me they think I am full of shit and I can tell them the same.
Now, you can certainly overdo it. For example, if you're telling people to SHUT THE FUCK UP on your developer mailing lists, it's possible you have gone too far.
But the vast majority of teams have the opposite problem: people filter their thoughts too much. The psychological and social incentives to do so are quite strong: we don't want to go against the team, or we're worried about giving offense, or we don't want to be "the bad guy." So team members might think individually, "We're driving off a cliff" or "That UI design is shit," but they either stay silent or the words that come out are so saccharine they mask the bitter truth below.
And that has a corrosive effect on culture. Those negative thoughts don't go away, and when team members repress doubts, resentment builds. Passive-aggressive behavior starts to predominate, politics brew, and problems linger on without being solved. So although people may hold their tongue intending to be nice, the result is that a more subtle kind of meanness takes root.
Actively fostering a culture of "no filter" is painful at first. But like exercising, the more you do it, the easier it gets. And it's better than the alternative—death.
How to break past filters on your team
So, where do you start?
You can’t just start telling your teammates they’re about to drive off a cliff. Or that they’re moths for bad ideas. If you do that, you’ll just end up with a bunch of defensive, insulted, or angry co-workers.
So I don't think most of us can create "no filter" behavior as a speaker alone. I think "no filter" has to start with us opening up as listeners.
In particular, teams can start to break down their own filters by asking themselves the hardest question.
In the first week of Y Combinator, Paul Graham told each startup in our batch to ask him "Are we failing?" It's a question that cuts to the bone, and most of us never asked because we were afraid of the answer. And therein lies the trick: we didn't really need Paul Graham to tell us where we were failing. We already knew, and we were simply deluding ourselves. What we were missing was simply the courage to ask ourselves the hardest question, and stop filtering our own answers.
Even if your startup is 'killing it,' there's always some area where it's failing, some muffled doubt that silently gnaws at people.
So if you want to break down filters on your team, start by asking : "Are we failing? How?"
And just listen.
Update: HN Discussion
Thanks to Christine Yen, Garry Tan, and Kalvin Wang for reading drafts of this... and having no filter at all.